Cuphead and the Gals
by NomadicInterests
Summary: Cuphead and Mugman embark on their journey to collect the contracts of the Devil's debtors to save their own souls and along the way, Cuphead bangs the chicks behind Mug's back. Cuphead x Girl bosses and some girl npcs. Rated M for MANY LEMONS.
1. The Fish and The Cup

**Cuphead and the Gals**

 **Chapter 1**

 **The Fish and The Cup**

Once upon a time, in a magical place called Inkwell Isle, there were two brothers named Cuphead and Mugman. They lived without a care under the watchful eye of the wise Elder Kettle. One day, the two boys wandered far from home, and – despite the Elder Kettle's many warnings – ended up on the wrong side of the tracks and entered the Devil's Casino. Inside, Cuphead and Mugman soon found themselves on a winning streak at the Craps table.

" **Hot dawg!** " exclaimed King Dice, the casino's sleazy manager. " **These fellas can't lose!** "

" **Nice run, boys,** " laughed a newcomer.

The brothers gasped. It was the casino's owner – The Devil himself!

" **Now, how about we raise the stakes?** " he suggested with a toothy grin. " **Win one more roll, and all the loot in my casino is yours!** " the Devil boomed. " **But if you loose, I'll have your souls! Deal?** "

Cuphead, blinded by easy riches, nodded and grabbed the dice for a throw.

" **Good gosh, Cuphead, no!** " cried Mugman, for he understood the danger.

But it was too late!

" **Snake eyes!** " laughed the Devil while slamming the floor. " **You lose!** "

The brother trembled in fear as he loomed over them.

" **Now, about those souls...** "

The brothers pleaded for their very lives.

"T **h-there must be another w-way to repay you,** " Mugman stammered.

" **Yes, p-please, mister!** " Cuphead added.

" **Hmm, perhaps there is,** " the Devil snickered, pulling out a parchment. "I **have here a list of my runaway debtors. Collect their souls for me, and I just might pardon you two mugs.** "

" **Now get going!** " The Devil roared, kicking the boys out most rudely. " **You have 'til midnight tomorrow to collect every one of those souls! Otherwise I'll be the one collecting yours!** "

Cuphead and Mugman were terribly frightened and ran away as fast as they could.

" **C'mon, Mug!** " panted Cuphead. " **We have to find Elder Kettle. He'll know what to do!** "

When Cuphead and Mugman returned to Elder Kettle, they filled him in with worry very present in there tone. He understood and gave them both magic power to help collect the contracts and with that, he sent them off. And so they did, setting off as fast as they could. Beating bosses left and right, the root pack, Mr. Blobby, the froggy fighter bros, until they discovered a mausoleum. There was a fish nearby so they decided to ask her for info.

"Begone, spirits!" the fish said, taking a fighting stance.

"Wait!" Cuphead and Mugman said, throwing there arms up to defend themselves.

"Oh, wait… You're real. I was about to you with the ol' parry move! That's how you deal with ghosts 'round here." The fish explained, sitting back down.

"There are ghosts around here?" Mugman asked, trembling a little.

"Yeah, some say that there mausoleum is haunted. Only a nitwit tries shootin' someone who ain't really there." she said like everybody knew it, which everyone did know.

"Pff, yeah, kind obvious." Cuphead said.

"What is also obvious is that you should use a big worm to catch the good fish, if you catch my drift." She said, Cuphead following her gaze. "Speakin' of not bein' places… would you fellas mind movin' on? You're spookin' the fish."

"Yeah, sure, we'll scoot." Cuphead said and started walking towards the mausoleum. "Hey Mugman, why don't you go scout the building, see if what she is saying is true. If you need help just holler, I am going to go see if I can get more info out of that fish." he said, coaxing Mugman.

"Ok, but make sure you come as fast as you can!" Mugman requested, heading away from his brother.

"Oh I will." Cuphead responded, heading back to the fish. "Hey there, I can help you fish, got a big ol' worm, right here." He told her, reaching in his pant to pull out his rather hard worm.

"Mmmm, this looks like it will do nicely, let me test it to make sure." She said, taking in the aroma of his cock.

She opens her mouth wide and takes the worm into her mouth, licking the tip carefully causing Cuphead to moan. "This worm sure looks like it will work, I just need to know if it will help me catch and _release_." With that, she began to slowly bob her head up and down, working on his shaft as he continued to moan and moan. Soon, she was sucking him off hard.

"Oh god I think I'm going to BLOW." he said as he shot a hot load into her mouth.

"Yummm, that was the best, cum back any time, I could use your help with fishing again." She said as he got cleaned up.

Right about that time, Mugman's call for help reached his ears so he dashed off to help him. He entered the mausoleum and ran to Mugman's rescue. He was surrounded by ghosts and was cowering in fear. These ghosts looked mean but would be no match for a parry.

"Mugman, try to hit them with a parry!" Cuphead said, jumping up to do the same.

Mugman tried to do it, but still shaking heavily from fear, failed to do so, hitting his head on the stand holding an urn and fell unconscious. Cuphead panicked but kept his cool as he raced to save his brother and the urn the ghosts were after. He gracefully parried ghost after ghost, dashing to the next, even hitting multiple ghosts before landing. Finally, it seemed like all of them had gone so Cuphead ran to check on his brother. He was alright, just unconcious. The urn began to shake and the lid flew off. Out came a beautiful ghost.

"Gosh, I don't know how to thank you boys for saving me! Where are my manners? I didn't even introduce myself! I am known as the Legendary Chalice, pleased to meet you." She introduced.

"Well I am pleased to meet you, it not every day that a cup like me gets to see a sexy cup like you." Cuphead smoothly replied.

"Why thank you, I was searching for magic and I got trapped by ghosts! Speaking of magic, please accept this gift, it should help! Is there anything else I can do for you?" She asked.

"Well, there is one other thing..." Cuphead said, pulling down his pants to reveal his cock, which was already huge in its limp state. "My brother will be out for a couple hours it seems like, so what do you think? Wanna go a couple rounds?" He asked.

She started to tremble, thinking about that tasty looking cock. She hasn't had one for nearly 100 years since people were to afraid.

"S-Sure." She stammered. "All I need you to do is cum for me. You may not have known this but cum has magical properties. For me, it would allow me to sustain a human form for a while." She said.

"Oh, I can do that. So then, why don't you take off your clothes and put on a show for me?" He asked, sitting down in a comfortable position.

With her back to Cuphead, she enticingly took off her clothes slowly, taking glances back at him with sexual expressions. Once stripped, she began messaging her left boob, while taking her right mound into her mouth, moaning in the process. This display was more than enough to give Cuphead a large, raging boner, so he began stroking his member. Chalice continued her show, trailing her left hand down to her pussy and spread her lips, revealing that she was very wet. She spread her legs further as she started to rub her cunt. This turned Cuphead on even more as he began to furiously work his hand up and down his rod.

"Oahhh, I'm getting close." He warned.

Chalice leaned over his cock, mouth open, waiting for his cum as she continued to rub her clit. Cuphead moaned loudly and let loose his thick, milky white juices. Chalice groaned as she was coated in said juices. Right, before his eyes, she materialized falling a slight distance, cock going straight into his mouth. She swallowed the last of his cum, savoring the flavor.

"Alright, lets fuck!" She said, positioning herself on top of him.

"No, not yet." Cuphead interrupted, quickly flipping there position. He moved down her body, planting tender kisses until at last he reached his target area. "First, I want a taste of this pussy." He told her, sniffing her cunt.

He licked his lips and started treating the area around his target, like a predator stalking its prey, creeping up on it slowly before it moves in and strikes. Chalice quivered at the feeling but he had only begun. He spread her pussy lips and took in the sweet smell, before diving his tongue in. Her whole body shook with pleasure as she cried out in please. He smiled and continued to explore her insides, drinking her sweet juices. She continued to shake harder and harder by the minute.

"ahhh, ahhh, ahhhhh, I'm cumming!" She moaned, splashing Cupheads face in her sweet, liquids.

"You taste good," He said. "Ready to continue?" He asked. Just then, Mugman began to stir.

"SHIT! Hide!" Cuphead ordered, quickly slipping into his clothes.

Chalice rolled off the stand to the other side where she wouldn't be seen. Mugman blinked his eyes open, vision blurry.

"Ugh, what happened?" Mugman groaned.

"Thank goodness your ok!" Cuphead praised, internally hating that he woke up right when he was going to bone that sexy cup. "You missed the ghosts and banged your head on that table. I defeated them all and a friendly ghost gave us a new super ability."

"Woah, what? That's weird, also you smell." Mugman noticed.

"Uh, yeah, those ghosts had these weird slime that got on me, I need to wash myself."

"Oh that makes since, well I am sorry I've been sleeping on the job, we need to get going!" Mugman said, getting to his feet.

"Yes we do brother."

And so the two brothers set off to the next their next destination. What evil beings lay in wait for them? What people will Cuphead fuck next? Will he succeed in fucking more girls? Will the two brothers collect the contracts before the deadline? Find out in the next chapter:

 **Chapter 2**

 **Sugar Tits and The Blimp!**

 **This fanfiction was created by me, Dragonpow23, I only post on so if you see this fanfic anywhere else under someone also named Dragonpow23, it is a fraud. This chapter was made and published on 10/30/17**


	2. Sugar Tits and The Blimp

**Cuphead and the Gals**

 **Chapter 2**

 **Sugar Tits and The Blimp**

So the two brother continued onward, to a giant tree. There they carefully made their way to the top, dodging birds, parrying caterpillars, vanquishing bugs, and chopping trees. Once at the top, they witnessed the horrors of taking part in homicide. They needed to jump on the leaves of bugs to progress but someone didn't want them to and killed the bug after they stepped on it. Eventually they came across the foe. A large wasp/dragonfly, spitting fire! They frantically moved from conveniently-placed bugs to coincidentally-placed bugs until they killed the said foe. Taking a leap of faith, they continued onward! Their next target, Cagney Corruption, the weed from hell. He was a tough one, but the boys somehow triumphed over the fire colored Flowey. That was one more checked off the list, and one remained of their homeland.

"Where is the last one? I have looked at this map like a hundred times over and I can't find it!" Cuphead shouted in frustration.

"You know, its probably around here." Mugman pointed to the blotched out part of the map. "It would be easier to know if someone wasn't impatient and waited before the bug guts finished falling before dashing through them." He reminded.

"Yeah, Yeah, I know. Well anyways, that means we will have to back up by the blob guy. Maybe a pathway opened up that we didn't notice?" Cuphead suggested.

"That would probably be it." Mugman agreed as they started back with a feeling of hurry.

And hurry they did, past Axeman, past the damn tree, past Porkrinds Em- actually, they stopped at Porkrind for a quick pick-me-up and to buy new weapons. After that, they booked it straight for the path they didn't take after beating Mr. Blobby. They hiked uphill before coming to halt as they came upon a cliff. In the distance an area was seen that was most likely the place where they needed to be. They began brainstorming ideas.

"Maybe we could build a bridge!" Cuphead suggested.

"Nah that would take too long." Mugman shot down.

"What if we flew over?" Cuphead came up with.

"In what plan-"

"What's that? You two want to fly in a plane like I do? Ha!" laughed a nerdy looking canteen the brothers hadn't noticed before. "You're not sitting in any cockpit 'til you study those blueprints!" He said, pointing to a plaque with blueprints that stood next to the cliff.

"Ok..." Cuphead said awkwardly as his brother and him went to take a look at the blueprints.

After about a minute of looking at the blueprints, the canteen came back over.

"You two are READY! And I built a bridge while you were studying that!" he said, scaring them from deep concentration.

"What? How? Also, we barely looked at it!" Cuphead and Mugman said in unified confusion.

"Don't worry, knowledge sinks in very fast, and why a bridge that was? Cuz FUCK IT, this story needs progression! Have fun and good luck!" The canteen explained, wandering off.

The brothers shrugged and continued forward, trying not to let that 4th wall break bother them. As the approached the next target, they saw the planes were needed for Cuphead and Mugman were up against a flying foe – Hilda Berg! As she inflated herself, the boys had a hunch they were in for a rough fight n flight. And a rough one it was! Having just learned to fly, it was big step since now they had to deal with minions, materialized laughs, and enemy bullets!

After a while being shot by bullets, Hilda began to inflate. ' _We beat her! She is gonna pop!_ ' the boys thought, but they were very wrong. She deflated, spewing clouds from her mouth that covered her body. Out of those clouds came a raging bull! They were taken by surprise but kept their cool. The brothers managed to force her back into blimp form and the point of changing again. But this time, out came two hot cloud sisters. Their jugs were big and squishy looking, and perfect, asses; round and firm but jelly like which would feel great to slap. The clouds only covered what was needed and little to the imagination. To top it off, the sisters were squished together in a pose that made them look like lesbian. At any moment, they could kiss and finger each others clits.

This gave Cuphead a mighty boner that ached to be satisfied. Maybe he would go fuck that fish again but for now, he needed to deal with her. The duo continued the relentless attack until she turned into a FUCKING MOON that launches UFO's with alien space lasers but they managed to finish her off. She turned back into humanoid form and floated to the ground, into a forest. The brothers landed nearby and got out of their planes.

"I have an idea!" announced Mugman. "We'll save time if you go collect the contract from her body and I take these to Porkrinds to get fixed up."

Sounds like a great idea bro! I'll go search for her now!" Cuphead agreed, setting off into the forest. ' _Yeah, sure, send me to look for her._ ' he thought, feeling annoyed.

It didn't take him long before he found her. He searched her for the contract, finding it before too long. Cuphead turned to leave but then he noticed small but petite tits and a wet skirt belonging to the blimp. ' _Well hello there._ ' he thought to himself. HE walked over to her, getting down, close to her cunny. He spread her legs and pulled down her skirt. Her panties were soaked in her sweet smelling juices. He discarded the skirt and slid the panties off her legs the same, taking time to sniff the smell once again. He stuffed them in his pocket as a souvenir, a weird one, but definitely something he felt was worth keeping.

Moving on, he leaned down and started licking her cunt, occasionally touching over her clit. She was quivering like crazy. Cuphead chuckled and continued to slurp up her pussy juice until he had his fill. He took out his cock and aligned it with her entrance. With on switch motion, he was inside her and started pounding away. She started moaning loudly, hands reaching to pleasure her self further. She started rubbing her clit and pinching her tits while still unaware of her partner.

"Ah, faster, faster, pound me faster!" She moaned out.

Cuphead began pumping in and out of her as fast as he could. He began moaning too as he was close to his limit. She began to squirm again signaling that she was also about to burst. As he was about to cum, he pulled all the way out to the tip and slammed himself back in, cumming in unison with Hilda. A little weak from the boning, he fell forward onto her. Regaining his energy quickly, he got up, redressed, and walked out of the forest to find his brother. They ran into each other at the big tree.

"Hey, great timing!" Mugman said, seeing Cuphead. "Did you get the contract?"

"Of course I did, here it is." He said, presenting the contract.

"Great, now lets hurry up and get to the next island before it too late." Mugman said.

The brothers began the walking again, away from the tree. The Axeman stepped aside, revealing a golden coin. He said it was a reward for their troubles. They continued walk, past the meadow with that dreadful flower and to a die house. Once there, they pushed open the doors, meeting King Dice inside as the doors slammed shut behind them.

"Well, ain't that a pip!" He greeted. "Looks like you really put the kibosh on them debtors. You can head on over to the next isle. Plenty more marks for you to lean on there!" he explained.

After he finished, he twisted, disappearing into the floor. The duo shrugged for the second time this chapter and continued forward. They pushed through the doors on the other side of the house and walked into the next area. It was a carnival like area! There was a Faris wheel, a rollet coaster, tents, a cake house…. OOO! A cake house! The boys, giving into their impulse for a moment, ran over to the cake house.

"This looks yummy!" Cuphead said, beginning to stuff his face.

"Yeah but you gotta try this!" Mugman responded.

Suddenly, the candy cane gates of the house flung open, a large candy cane shot out, grabbing Cuphead by the neck. He was jerked inside the house and the gates slammed shut while a flying waffle came out. Mugman dropped his sweets and began shooting at the waffle, shocked but determined to get his brother back. Meanwhile, inside, Cuphead furiously trying to dodge his attacker. As he moved around the house, he caught a the savory and delicious smell of his female pursuer, that rose above the rest of the other powerful smelling sweets. She looked to also be made of sweets and tasty treats.

Suddenly becoming horny, Cuphead got an idea of how to sleep with her. He ran straight for her, and then fell on his back to go into a slide. He slide right under her dress and made a quick, and well aimed shot to her panties, just powerful enough to eradicate the fabric. He quickly got up and turned around, dashed towards her again while she was still dazed. He lifted up her dress and stood on his knees as he looked at her pussy. She began to drip, probably know what was about to happen and couldn't help but become horny herself. He reached up and began tonguing her cunt.

"H-hey! S-stop that!" She said, about to reach down and beat him but changed her mind and pushed his head in further.

"mmmmmmmmm. Ahhh." she moaned.

Cuphead began to search her insides more vigorously, desperately wanting more of her juices. She began moaning louder and louder until she came in his face, dispensing sweet milk. He moved on, laying her on her back. He moved up to suck on her tits which were the sweetest thing he had ever tasted. They were big and squishy too. Bigger than Hilda's, by a lot. She was very sensitive there, starting to louder than when he was eating her out. She actually started lactating sweet milk. He stood up, stopping all pleasure, making the baroness look up at him longingly.

"I've you all the treats up until now. If you want more, you'll have to work for it and treat me." he said.

She took the reigns and pushed him onto a nearby giant gumdrop that served as a seat. She hastily pulled his pants down as his large candy cane popped out like a spring. The baroness licked her lips as she imagined having that large cock in her sweet peach. She started out by licking up and down the sides of his rod, then going to tip. She swirled her tongue round and round. Then… she dove in, gagging as she took it down her throat. Cuphead moaned loudly as she went up and down his shaft.

"You want a real treat? Then let's take this to the next level." She said, lubing his cock up.

She put her enormous breasts around it and to service him. Her giant jugs went up and down his candy cane. She licked the tip each time it came close to her face and began to work her pair faster. She eventually started giving him a blow job as well as a titty fuck. He couldn't help but begin to thrust his hips and let out a load moan as blew his load straight into her face. She stuck her tongue out, getting as much as possible. Not to her liking, working her large breasts like that, plus the pleasure from earlier knocked her out before she could get his dick in her pussy.

"Don't worry, I'll be sure to fuck you from behind next time we meet." Cuphead said as he got cleaned up.

He then walked out of the candy house, smelling like candy of course that masked the usual smell of hot sex. His brother ran over to him, overcome with joy since he thought he lost his brother. Cuphead made up a tale of how he defeated the Candy Queen from within (her pussy but he left that out). The two regained their breath and headed onto the next debtor. Who will Cuphead fuck next? Will he keep his word and revisit Miss Sugar Tits? Will Mugman find out? Or will he conveniently get separated from Cuphead so his brother can fuck another girl? Most likely so. Find out in the next chapter:

 **Chapter 3**

 **The Bitchy Bee and Sexy Cala Marie**

 **(I know its Maria but rhyming made it better)**

 **Don't forget to fave and follow, as well as review if you enjoyed this chapter (as well as yourself) and want to see more. This fanfic belongs to me (Dragonpow23) and originates and stays on , if you have seen this fanfic on any other website, it is a faker and is not me. See ya next time!**


	3. The Bitchy Bee and Sexy Cala Marie

**(A/N) Thank you all for taking time to read this. Sadly, someone has beat me to the punch in creating a lemon with Cala Maria but I am pretty sure mine will strike a harder blow. Anyways, read on and enjoy! (←This was written in the middle of making the Cala Maria section!)**

 **Cuphead and the Gals**

 **Chapter 3**

 **The Bitchy Bee and Sexy Cala Marie**

After defeating the Candy Queen, the brothers went on to beat many other debtors **(none of which he fucked because Sugar Tits is the only female in world 2)** such as the Red Magic Fuck, Two-Face the Clown, Pinocchio the Bird, and Flamethrower-Head Hydra. All were difficult battle, fought with dread but they managed to best all of them, collecting all of their contracts as well. The also beat the fair grounds and took the coins they won from the mini-games and stocked up on life saving crap. Cuphead's personal favorite was the "Don't-Need-To-Look-Back" potion, A.K.A. the roundabout. Now that you are up to speed, we will join the boys as they walk into the next Die house to move onto the next area.

"Looks like I mighta underestimated ya, Cupface." He insulted. "You gave it to them debtors but good!"

' _He must know I have been doing some fucking..._ ' Cuphead thought.

"Go on over to the next island, Lotsa fun times waitin' for you there! Ha ha ha!" He joked, before disappearing into the floor again.

"Well that was weird." Mugman stated as they pushed through the door to the new section.

"Yeah, that was!" Cuphead nervously agreed.

' _That creep, I know I am a pervert for doing the fucking but he knew somehow._ ' he thought, trying to hide his worry.

 **(A/N) I won't lie, when I watched a video to see exactly what King Dice said as you entered world 3, I was surprised to see that is coincidentally lined up with this fanfic perfectly!**

The brothers followed the map until they reached an extremely tall, yellow building. A very loud buzzing could be heard before they were even within 20 feet of the door. The brothers looked at each other with worry, neither one of them was fond of bugs especially bees. But they had to get the contract or else they would be slaves of the devil. When they got in, they found themselves in a neat lobby with the smell of honey filling the air. An elevator dinged and a large bee in a blue uniform stepped out. On his shirt was a label that read security. He spotted the duo and panicked.

"It's the to cups! They are here! Protect the queen!" He said into a walkie-talkie.

He then hit a button and the entire building collapsed. The nice lobby turned into an empty warehouse. Every floor on the ceiling collapsed so the building was now just a giant box. Honey started pouring in and filling up the floor. The guard caught his foot in it and struggle to pull it out telling the brothers that if they fell in, it would be over for them. Thankfully, there were platforms along the wall where the floor didn't didn't get destroyed so they would be able to escape the lava-like honey. The guard managed to free himself and began to fight the brothers as they began scaling the wall. From there past experiences, he was nothing. They took him down easily, and the same happened for the next 2 guards that tried to stop them. They expected another guard to come in the last ones place but the next bee to come in was definitely not a guard. It was the Queen Bee herself!

She was much stronger than the brother anticipated. They struggled against her, having a handful of close calls. But then she finally prevailed when Mugman lost his footing and stumbled. Cuphead leaped down to help, dropping his guard so she moved in. She quickly encased Mugman entirely in honey that hardened. She treated Cuphead differently, only trapping his arms and legs. Cuphead knew what would happen. She would probe him for information, tear him slowly apart, wrap those pieces in wax, and use them as food for the next generation. She flew closer to him as he flinched, waiting for the torture to begin.

"So it is you." She said calmly. "The cup that is rumored to give a great fuck."

Cuphead opened his eyes and stared at her in confusion.

"You looked surprised. You didn't think that word wouldn't get around?" She chuckled.

He didn't know what to say since he honestly never considered that. He wondered if his brother knew.

"I think since you have presented yourself to me, I'll confirm if that rumor is true or not." She said, flying closer to him.

"Please, do anything to me you want, just let my brother go." Cuphead pleaded.

"Don't worry, if what the rumors say are indeed true, I'll let you both go and give you my contract." She said, her face right in front of his crotch as she stared lustfully into his eyes.

She reached over and pulled his pants down, revealing his cock, which was limp.

"ooo, this does look yummy."

She began to lick the cock until it was to full hardness. She continued polishing it as Cuphead was moaning once again. Round and round her tongue went until she decided it was time. She stuffed the 12 inch meat rod as far in as it could go before slowly pulling back. She started picking up her pace as Cuphead enjoyed himself. He finally couldn't take it anymore and burst in her mouth. She swallowed every ounce of it. By now, she was very horny and was fingering herself but she knew it wouldn't be long before her subjects saw her so she decided to let him go and actually part him with one more gift. His cock was already large but she decided, with her witchery skills, to make it and 16 inch cock. Of course, he would have to come back and use it on her but his fame would also raise with the ladies.

"Well, the rumors are true, you are free to go. You and your brother will be transported outside, only with my contract. But you must promise to come back and give me more attention." She proposed.

"S-Sounds like a deal to me, your highness." he accepted, still enjoying the pleasure.

She chanted words he couldn't understand and the next thing he saw was the front door of the building. His brother was by his side, recovering from being trapped inside an oxygen lacking cocoon. Cuphead held the queen bee's contract in his hand, feeling kind of sad he only had a quick blowjob but was internally proud his above average dick already has him the ladies pants before he even meets them. He turned his attention back to his brother, giving him a moment to rest before making up another story of how he beat the enemy.

"I am sorry bro, I am just not as good as you." Mugman apologized, feeling like a burden.

"Don't be like that! Your help is really…. Helpful. I know if I was on this journey by myself, that I would not make it. So come on, we have more debtors!" Cuphead encouraged.

So the two continued on wards. First they had a weird battle with a rat and cat. When the cat surprised them by devouring the rat, the boys thought they were saved! But then the cat turned on them! Next, they trekked through a dangerous port filled with sea creatures and went on to battle a narwhal ship. The fight was hard since the ship kept firing lazers but that still didn't stop them. It did however exhaust both of them. They couldn't waste anytime but if they didn't rest from this non-stop fighting, they would both perish. Still, they had to rest and asked for a rental room at Porkrinds.

"Cuphead, one of us need to collect another contract while the other rest. I have this potion that can restore stamina and I think you should have it. You need it most." Mugman urged.

"Why can't we split it? You know I need your help and you need mine!" Cuphead reasoned, not sure if he could do it.

"Don't be silly, you will be able to do it. Besides, if we split it, it won't have any effect. Now go!" Mugman insisted, giving Cuphead the potion.

Cuphead reluctantly drank it and said his farewell before heading off to collect the next contract. He really did need the potion for the next battle wouldn't be one of strength but one of endurance sexually. He headed out from Porkrinds toward the destination of the next debtor. He heard from the locals that this debtor loves the sea so he would probably have to fight him/her in his plane so he dragged it along with him. Eventually, he came to the shore line, taking a moment to breathe in the salty air and admire the sea. He could probably sit there for hours, listing to the waves but that contract wasn't going to collect itself. He hopped in his plane and took off.

After flying for a while, Cuphead spotted a relatively small looking island. It had a flat, smooth surface made out of rock, wet from the ocean spray, being only 5 ft above its surface. Then there was large hill blocking the view of the other half of the island. He thought it would be a good place to land and maybe take a stretch break. His plane was built for durability and use, not for comfortableness, so he was a little sore. The landing was a bit rough but not one of his worse landings. He jumped out and began to walk around, feeling relieved to be out of the constricting hunk of metal. Wanting to investigate the other side of the island, he walked towards the hill, discovering a tunnel carved into the side. He walked carefully through the tunnel, as light quickly faded away, having to feel his way around at times. Sounds began to echo through the tunnel, sounds that were hard for him to make out since the walls of the tunnels seemed to distort it. As light also began to appear, the sounds became more clear, sounding and awful lot like moaning.

Cuphead slowed his walking down, not wanting to be spotted by whoever was at the end of the tunnel. When he did reach the end of the tunnel, he was amazed by what he saw. It was a cave/cove. The cove had an almost perfect circle pool of water, with a small connection to the sea. Waves calmly washed up the sandy beach. There were a few large rocks here and there but nothing too much to worry about. But it was also nicely shaded. The ceiling of the cave went about 20 feet over the water giving the beach some nice shade. But of course, Cuphead took all of this in… after her saw the giant fucking mermaid resting partly on the sand, and partly in the water. She was deep into her session of self pleasure, very unaware of Cuphead's presence. Still, Cuphead backed up into the tunnel to conceal himself, and his boner.

This giant mermaid was giving the a good show, fingering her pussy under her scaly dress, as she massaged her breast under her seashell bra. She pinched her clit a bit, letting out moans of pleasure. Cuphead couldn't resist any longer, he pulled out his cock and began stroking, paying too much attention to her to notice his enlarged rod. Although, things changed suddenly as he noticed shimmering in the water. Many eels popped out, wrapping around the mermaid goddess and beginning to rape her. She gasped in surprise, before succombing to more moaning as they fucked away at her. They were wrapped around her tits, sucking them, ramming their tails into her mouth, teasing her pussy. But she started shrinking in size, shrinking and shrinking until she was normal. As quickly as the eels appeared, they left.

"Fucking eels, stole my fucking magic!" She swore. "And I am even hornier."

Cuphead couldn't seem to control himself as her walked up behind her, not so scared now that she was not so giant. His dick felt so hard that it hurt and all her wanted to do was fuck this lady.

"Well maybe I can help you." he said.

Startled, she turned around, his head inches away from her lips. She looked up at him with lust and he returned the gaze, also with lust. Her gazed returned to this cock presented before her, reaching her hand up to feel it. It was so firm, so erect, ready for a long session of fuckery.

"Yes, I think you can, but, you dick is so big. I'll really enjoy it." She said, before beginning to stroke it, with her soft hand.

She pushed Cuphead over, sitting between his legs and stroking his rod with both hands. She took her time, feeling up every part. She started to lick his tip, swirling her tongue around it occasionally before she took him into her mouth. She fondled his balls while still stroking him with one hand as she began lowering her head down. She gagged and coughed as he hit the back of her throat before slowly pulling out, making a pop sound as she sexily looked at him. She slowly sped up the pace, starting to suck his dick like candy. She repeated this process for several minutes before taking him by surprise and engulfing his entire length. Her mouth felt the best as he moaned and moaned. The combination of her sucking and stroking his dick, while she fondled his balls, was more than enough to push him over the edge. Without warning, he blew his load down her throat. There was so much the cum exploded out of here mouth, leaking down his length. She came up, coughing and hacking before frantically licking up his delicous cum that had spilled.

"That was great, you are the best cock sucker I have ever had. My name is Cuphead." He commented, realizing he had not introduced himself.

"I am Cala Maria, and its your turn to pleasure me, if you do good, I'll bust your nut with these great tits of mine." She proposed.

Cala Maria slipped off her scaly dress, revealing two slender and smooth legs, just as pale as the rest of her beautiful skin. She spread her legs and her pussy, using her other hand to motion a seductive finger at Cuphead. Not needing to be told twice, he hungrily crawled up to her pussy and began licking it, teasing the outside. His tongue eventually ventured to her folds, already encased in her sweet pussy juices from the teasing. He finally shot his tongue inside her, making her arch her back in ecstasy and crying out in pleasure. He carefully explored the insides while reaching a hand under her seashells to play with her glorious mound. She tasted amazing, even better than Miss Sugar Tits, and her insides seemed to be shaped perfectly for a good fuck. Having explored enough her removed his tongue, causing her to whimper in disappointment even though she knew what he was going to do next. He inserted his finger, slowly moving it in and out before going into a vigorous finger fuck.

"Oh, oh, oh, yes, yes, yes that's it! Ahhhhh!" She moaned, crying as well as she came, soaking his finger in her juices.

Before she could move, he sat on top of her, ripping her seashells off. He grabbed her tits and fastened them around his cock. He began to thrust his dick in between her tits, pressing the tip against her lips. She reached her tongue out, licking his member every time it came close. Before long, Cuphead scooted forward a bit to have a titfuck n' suck. Cuphead felt like he was in heaven, his erect rod between two milk jugs of gold, thrusting into the mouth of a goddess. Cala Maria began helping out even more, taking hold of her tits and working them faster, as well as sucking him off and swirling her tongue around his cock. Cuphead suddenly moved forward, getting on hand and knees, and aligned his spear with the mermaids mouth.

With his legs by her head, he took her by surprise as he slammed forward, forcing her into a deep throat. She gagged pushing him out but he resisted and slammed her head again before she got his entire length out. She eventually recovered from shock and started breathing though her nose and stopping her gag reflex. Cuphead continued to slowly pull out and then quickly slam himself back in, with Cala Maria enjoying the sensation of her throat being tickled. Although she was good at holding her breath for long periods of time, she was coming upon her limit. Fortunately, Cuphead was also cumming upon his limit. He slowly pulled out all the way to the tip, and slammed himself back in as hard as possible. This set him off as he blew a big load into her mouth, and with that, he fell side ways, breathing heavily while she swallowed his cum before gasping for air.

"Wow, that was great, it surprised me but I'd wouldn't mind doing it again. I like man with some force." She commented, turning on her side to face the recovering Cuphead. "You're not worn out, are you? We haven't started the main course!"

"No, no! I'm fine! I'm just… your throat is amazing, you wiped me out for a bit." He reassured, in between pants.

"Well then, what are you waiting for? Get over here and fuck my pussy!" She teased, twisting until her vagina faced Cuphead.

She bent her knees, spreading her legs, and using her hand to once more spread her pussy lips. Cuphead hurriedly scrambled up, crawling over to the hot babe of a mermaid, leaving the door wide open for him to come in. He stood up on his knees, holding his cock in hand and gently rubbing it at the door which she closed, teasing him to bust it down and rob her. He continued to rub around the entrance, taking his sweet time to tease her, making her grow hot and impatient.

"JUST FUCK ME ALREADY! PLUNGE THAT COCK IN AND FUCK ME INTO OBLIVION!" She ordered, feeling irritated.

Cuphead chuckled and gradually began to push a little more before he parted her pussy lips and began to insert himself. Cala, thinking he was big before, panicked! Just from putting the tip in, she knew that her throat lied to just how thick he really was. He continued to leisurly insert is dick, still only a half an inch in. She was having a war in her mind, tell him, or have the time of your life and hurt the next week. She spoke up just when he was going to surprise smash her.

"WAIT! B-Be g-gentle. I'm still a virgin." She stammered, looking away with a face full of fluster.

"Oh, so your a virgin? Virgin…" He asked, repeating the last bit mostly to himself as he thought. _'Damn, she still has her virginity? First of all, win, but more importantly, TIGHT!'_

"Y-yes, so please be very gentle." she restated.

"Ok, I'll be as soft as I can." He said.

He continued to slowly insert himself into her, wincing at how tight she was. She grunted, biting her lip to keep from screaming. Tears were forming in her eyes, only 2 inches in. Cuphead saw how much of pain she was in and had an idea so he pulled out. Although she was glad the pain was over, it was out done by the disappointment. He moved over to her face, dick right at her lips. "Lube it." He told her.

She reached out and began sucking his cock passionately, thinking he wants another tit-job, but after a while he pulled out and re-positioned himself with her hole.

"It should go in a bit easier now." He explained, nudged his cock back in.

It did slide in a bit easier but it still hurt. This time he slid 6 inches in. She couldn't help herself but squealed in pain. She insisted her pull it out but he shook his head while she squirmed in discomfort. He finally got impatient and slammed himself inside of her, thinking it would be the fastest method. She was screaming now, crying a river of tears of pain. He silenced her with a kiss, not moving his member so her inner sanctum could adjust to the size of his rod. He made his kiss more passionate as he prodded his tongue at her lips, asking to come in. She accepted, still teary, and slipped her tongue into his mouth. They wrestled a bit, getting accustomed to each others taste, just like his P in her V.

Once she stopped whimpering, he began to slowly pull out, breaking away from her amazing kiss. Her walls clenched him tightly, very tightly, as continued to slowly move out. She still whimpered in pain but it wasn't as much as she was beginning to get use to him. Once he was at the tip, with the same speed, he went back in. They both moaned aloud, Cuphead because she was super tight on his thick, and long cock, and Cala because she was getting use to said cock. He rhythmically repeated this, knowing that this was true heaven. Although the titty blowjob was good, this was the true cake-taker. Feeling confident that she was good, he picked up the pace.

"oh, aaaah, oooh, _ooooohh_." The mermaid bitch moaned, enjoying it. "Faster, faster! Pound my tight little pussy! I am ready, I can take it! Fuck me till your spent, Cups!"

Cuphead pulled all the way out to the tip, letting it sit there. He grabbed her legs and rested them on his shoulders while settling his hands on her thighs, close to her waist. He waited a couple seconds longer, taking in the look of excited and partial horror on her face as she knew she was about to be deeply fucked. Without warning, Cuphead smashed into her, shooting his cock deep into her cunny and stopping at her G-spot. She squealed in delight, like a little girl getting a kitten as a gift, and actually came right on the spot. But he didn't stop there! As fast as he went in, he pulled out and went in again, stomping that pussy, not caring if she hurt or not. He fucked her like there was no tomorrow, causing her to orgasm multiple times. She held her own legs up as he leaned over, giving attention to her triple D size mounds. He sucked one of the tits while using his hand to play with the other. Simultaneously, he bit her nipple and pinched the other.

"Oh fuck, do that more, nibble on my tits!" She said dirtily, moaning in pleasure.

"Someones becoming a bitch." Cuphead commented, going to back biting.

Her walls suddenly tightened around his cock, sucking him in and making it hard to pull out. Cuphead moaned into her breasts from the extreme pleasure.

"So you like being called a bitch?" He asked, receiving tightening around his cock is response.

"Yes, yes! Ah, oh, call me a-, ahhh, bitch! I'm your bitch, fuck me harder." she said in between pants and moans of pure pleasure.

Cuphead pushed himself to thrust faster, causing her to orgasm another time. Cala lost track of how many times she came while he still hadn't cum once. He reached up and shared another passionate kiss with her, tongue mingling and moans colliding. Sometimes they had to break for air but went straight back to having sex with their tongues. Cuphead had been holding back as much as possible but was finally close to his limit. He felt it that this would be a big one, his biggest cumshot yet.

"I-I'm clo-close. I can't hold on much longer!" he warned.

"Then come with me!" She said.

Cuphead was pounding her harder than ever before, hitting her womb each time he thrust. His moaning became louder along with hers as they began saying each others names. He felt his balls about to burst so once more, he pulled all 16 inches out to the tip before slamming, balls deep, back into her. This set off an eruption as cum exploded out his tip, mingling with her climax. The hot come filled her insides and didn't just leak out but splashed out of her cunt. She fell backwards, experiencing pure euphoria. Her insides felt hot and he still wasn't done. Cuphead pulled out of her and stood up to cum all over her. He didn't even need to jack it off, there was still so much cum that it jetted out by it self. He covered every part of her in his hot, white, and delicious goo. There was cum on her legs, her belly, her arms her tits, her face, her octopus. And the cum was thick. But even after all that, it was still going. He put a tight grip on his dick to stop the flow, which hurt, but placed his cock in her mouth deepthroated her. She gladly accepted his gift and sucked as well. Finally his stream of cum ended.

"That was the best. I love you so much Cups." She said.

"You are the best fuck, I have ever had. I'll make sure to visit again. But I need to ask you a favor." He said.

"Anything for you." She promised, still in a daze for the best experience she ever had.

"I need your soul contract. Don't worry, I'll take good care of it. I am going to show that bastard devil what." He asked.

At first she was hesitant but put her trust in him. She told him where it was so he grabbed it and bid his farewell, promising to come back and fuck her again. He hopped in his plane began the flight back. He knew that out of all of the girls, he actually had a love for Cala Maria. She was the most sexy and the best partner. And so concludes this chapter! What will happen next? How is Mugman doing? Actually who cares about him? We are all here just to read the crazy fucks that Cuphead is having. But will Mugman ever join the party? Probably not but if so, how will the author screw it up and make everything awkward and make him probably want to delete the entire story as he has done in the past? Stay tuned for the next chapter:

 **Chapter 4**

 **An Ending**

 **Hello, thank you for reading this fanfiction and to this far. This fanfiction belongs to me (Dragonpow23) and it originates and stays on unless, I, myself post to other websites and confirm on here that it was me.**

 **I would like to thank lucienhalf58 for being the top (and really only) reviewer who has been some help, such as letting me know that Cuphead is now a category. Also, I am not writing this get fame, I write this fanfiction because no one else has written a good story yet and, myself included, need something like this to exist. I do, however, proudly hold the title as the first M-rated lemon fanfiction for Cuphead. I do apologize for the rushed plot in the first part with Rumor Honey bottoms, I mean, she is a bee, also I was really looking more forward to writing on Cuphead's and Cala Maria's encounter.**

 **Anyways, enough of my rambling, thank you for reading this 4,390 word chapter (longest chapter yet and that count excludes A/N) and remember to follow and favorite this story and me to get updates on any new chapters or stories I write. Don't forget to leave a review too! That will be all, catcha next time!**


	4. An Ending

**Cuphead and the Gals**

 **Chapter 4**

 **An Ending  
(xxx) (xxx) (xxxxx)**

With Cala Maria's contract in his possession, Cuphead hurried back to Mugman, making up a story of how he fought off the giant Mermaid. Mugman listened in awe and applauded at the end of the tale, then proceeded to get ready. The due then headed off to defeat the last few bosses. First they stopped by Dr. Wileyegg with his iron bucket, and opened him a can whooping oil in exchange _f_ or his contract. Next, they went on stage, with Mugman being the co-star and Cuphead being backstage crew. Clumsy as he purposely was, he 'accidentally' dropped a spotlight right on Sally's head. Being knocked out cold, she wasn't able to pay them so the brothers took their pay of 1 Sally Stageplay themselves and also excused said selves as well. Being in the hurry they were, the two boys rushed right over to the tracks. The positioned themselves about a mile away from the oncoming train, and began shooting the tracks. Their shots were so hot (no, not cum) that is melted the rails. They stepped back and watched as the excited-to-fight train was hurled off the tracks, becoming dent. Conveniently, the contract floated down for Cuphead and Mugman to collect. Having all of the contracts, the brother headed into the familiar cave to the casino of hell. They walked the red carpet, right up the stairs, pushing on a familiar do _o_ r. The devil was expected to be seen, but that sleaze-bag King Dice did the greeting instead.

"Well, lookee here! You actually pulled it off… but you made me lose a bet." He greeted, acting delighted to see them before his tone turned more on the serious side. "And for that, you ain't seein' the boss just yet. We're gonna play a little game fi _r_ st!"

Suddenly, the boy found themselves in a giant craps table. Had they been summoned into a giant world? No, as they looked around they saw the familiar decor of the casino along with a giant King Dice looming over the table. They chalked it up to being shrunk. Anyways, Cuphead saw the writing on the wall, literally. King Dice reached down and clapped a floa _t_ ing pink die into existence with numbers from 1-3. The duo agreed they were probably playing a Candy-land sort of game and timed their parries on the die just right. The whole fight was a joke, the mini-bosses were easy, they rolled 3 every time, and even King Dice was a cakewalk, no wonder he lost the bet. Now t _h_ at they finally defeated him, they walked over to the building on the other side of the casino, a tower of sorts with fancy doors. He must be in ther _e_ , so the boys barged right in, seeing their assumptions were right.

"Well, well, well… look how far you've come! Not only did you bust up my good-for-nothing lackey, King Dice..." He said, greeting them in the same manner as King Dice and also changing to a darker tone also like King _D_ ice. "...but I see you've got my soul contracts, as agreed! Hand 'em over, and join my team!" He demanded only to be told an obvious no from the boys. "Welching on me just like all the others, eh… I'll teach you for backing out of a deal – have at you!" he roared, fire behind his throne rising and roaring just like him.

He sat back in his throne as the boys began to shoot at him, while dodging the mini purple devils that hurled themselves across the room. He clapped before stretching his up high and then down to the floor and across the room like a dragon at a f _e_ stival. His head quickly snapped back into place, much like a measuring tape being reeled in. His horns grew until his head resembled that of a curly horned goat as his arms stretched from him and met each other in the middle. The boys jumped of his clap and shot at him in mid-air. His arms recoiled just as the boys landed and began shooting at him in a more comfortable angle. He tried once more with physical attack and decapitated himself, his head taking the form of a spider and jumping about at them. Not surprisingly, they survived. Knowing his stretchy attacks would never hit them, he began chanting words as painful bubbles appeared, before targeting the duo. He still couldn't hit them and eventually just jumped out of his skin, making a hole in the floor.

The boys were confused but saw the quickly growing fire and jumped in after him. They landed on floating platforms, the only ground available to them as a giant red de _v_ il sat before them, before he even had a chance to charge up an attack, they continued their barrage of bullets. His eyes joined together temporarily as he summoned an axe that looped in circles toward them. He also summoned multiple bat bombs to give them trouble along with flaming rocks that fell from the ceiling of the cave. When this didn't work, he became very angry, calling for giant purple demon guards that came down and spit skulls at the boys. He started crying like a baby summoning even more stuff, There was so much stuff on the screen that this author gave up trying to describe this fight. Sounding like a broken record, the boys defeat the devil.

The brothers had triumphed over the demon, forcing him to finally give up.

" **We shall accept your surrender, Devil,** " Cuphead laughed. " **But we're not done just yet!** "

And w _i_ th that, Cuphead and Mugman destroyed all of the soul contracts, releasing Inkwell Isle's residents from eternal servitude to the Devil.

" **Gosh, I can't wait to tell everybody!** " Cuphead said.

They boys set off for home, and at top speed.

" **C'mon, the last one there's a leaky cup!** " Mugman teased as they ran.

Once home, the brother gathered everyone together.

" **You're all freed of the Devil's debt!** " Cuphead announced.

" **And that fiend won't bother us again!** " Mugman added.

The Elder Kettle was literally brimming with pride as everyone began to cheer **(especially the ladies)** :

" **Let's hear it for Cuphead and Mugman!** "

" **Hip-hip-hurrah!** "

" **Hip-hip-hurrah!** "

As an a _l_ l-day celebration began, the brothers promised to never wand into trouble again. And they didn't – until the next time, of course! But that is another story…

 **The End  
**

 **Thank you so much for reading this story! As you know, I do not own the characters or the game but I do own this story, which originates and stays on unless I specifically say which site I put it on. Don't forget to review, and favorite/follow me and this story. Also, don't worry about Mugman, he is better of not knowing. See you until next time!**


	5. New Story! Check it out!

**Hi! Dragon here, no, I'm not actually updating this like many of you probably want. I am here to say I have made a new story for Ready Player One called Co-op Mode. I feel very proud with how the writing has come so far and fans of the book or movie that are following me might enjoy it as well. It is more story oriented instead of constant fucking like this story was but it will contain Z and Arty fucking each's brains out eventually. Anyways, sorry for possibly getting your hopes up of sally stage play but please go checkout and possibly fave/follow my newest story!**


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